Quantitative structure-activity relationships of ortho-aminomethylphenols and their derivatives

An Inverse Electron Demand Azo-Diels–Alder Reaction of o-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines

“…The presence of imino ether facilitates the generation of an o -QM from a quaternary ammonium salt 6 by partial deprotonation of the phenolic hydroxyl group. It should be noted that the acidity of quaternary ammonium salts is approximately 2.6–2.7 orders of magnitude higher than that of the corresponding Mannich base …”

“…It should be noted that the acidity of quaternary ammonium salts is approximately 2.6−2.7 orders of magnitude higher than that of the corresponding Mannich base. 15 At the same time, the reaction between 1-[(dimethylamino)-(phenyl)methyl]naphthalen-2-ol and methyl 4-benzimidate in DMF under reflux in the presence of NaI (1.5 equiv) leads only to naphtho [1,2-e][1,3]oxazine 3ca in 72% yield. Thus, the presence of a nucleophilic iodide ion and the protonated form of imino ether is necessary for the formation of a secondary amide.…”

Structure—bacteriostatic activity relationship for 2-aminomethylphenols and their ammonium salts

“…For example, a group of ten aminomethylphenols with variable substituents in the benzene ring exhibited a two-parametric correlation between the bacteriostatic activity with respect to St. aureus and their hydrophobic and induction constants of the substituents [1]. In another case [2], we used the steric constants of substi- Table 3). …”

“…Previous investigations have demonstrated that the biological activity of AMPs, their tertiary ammonium salts [1,2], and phenols [3] depend primarily on the hydrophobicity of substituents in the benzene ring of these compounds. Rather close linear relations of the type log(1/C)=f(n), where C is the minimum bacteriostatic concentration (e.g., for St. aureus), M, and n is the hydrophobicity factor of a substituent in the benzene ring, were obtained …”

“…The hydrophobicity factor (n) of radical R in the synthesized compounds (I -IV) was varied in a wider interval (rc < 8.5) as compared to that used previously for the calculation of parameters in equations (1) and (2), where n < 4 [2].…”